


Cherries, Chocolate, & Chances

by NegansOtherWife



Series: Tumblr Requests [3]
Category: The Walking Dead & Related Fandoms, The Walking Dead (Comics), The Walking Dead (TV)
Genre: Explicit Language, F/M, Food Sex, Implied/Referenced Underage Sex, Oral Sex, Smut, Teacher-Student Relationship
Language: English
Status: Completed
Published: 2018-07-07
Updated: 2018-07-07
Packaged: 2019-06-06 16:45:20
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,605
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15199076
Author URL: https://archiveofourown.org/users/NegansOtherWife/pseuds/NegansOtherWife
Summary: You'd thought you'd lost your chance. Time had pulled the two of you apart, but here he was and with that damn smirk, no less.





	Cherries, Chocolate, & Chances

**Author's Note:**

> I'm alittle slow to update my AO3 with the Tumblr requests I've had in the past. If you haven't read this one, you're in for a treat. x
> 
> My Tumblr: https://negansaysyouearnwhatyoutake.tumblr.com

It’d been just another typical day at Stone Bridge High, muggy and humid. The air practically dripped with teenage angst and its aggressive counterpart, testosterone. You and a small group of girlfriends, in an attempt to distance yourself from the suffocating atmosphere that came with over fifty teenagers condensed into one area, had sought shade atop the bleachers that overlooked the football field.

You’d taken a risk by not wearing a bra today during PE. You had to admit it was an emboldened move on your part, so blatantly brazen in fact, that the mumbled excuse of ‘female liberation’ was met with thinly veiled skepticism from even your closest confidant. Anyone with a pair of eyes knew of the dance that the two of you played. But it’d only been recently that you decided you wanted something _more_.  

Rolling your tongue so that the lolly in your mouth makes a loud ‘clacking’ sound against your teeth, you scan the approaching figure, knowing for a fact that your efforts will soon pay off.

“Coach Negan’s heading this way!” Heather, your best friend, warns shifting nervously in her seat. Always the goody two shoes, you’d had to coax her into ‘skipping’ PE. “Maybe we should go, Y/N? We’re supposed to be running laps.”

“Oh, honey.” You murmur, basking in the zap of electricity that runs the length of your spine when his eyes fall upon your peaked breasts. He swallows a bit heavily before addressing the small crowd of girls before him. “I’m just getting started.”

“Alright, ladies!” The muscles in his forearm bulge slightly when he claps his palms together. You think he’s only done that for your benefit when he catches your gaze, flexing his pectoral muscles before looking over your head. “Back to doing laps, you’ve had a long enough break.”

None of them move, and you mentally cheer on your friends for sticking to your plan. Even Heather who looks slightly nervous remains rooted to her spot. 

“Tell you what, Coach. If you can guess the flavor I have in my mouth…they’ll head back,” You say, beckoning to your mates with a coy smile. He returns it with one of his own, eyeing your breasts beneath the translucent fabric of your white athletic shirt. 

“Cherry,” He guesses, watching your reddened tongue lap at the sugary treat. 

You make a buzzing sound that signals he’d given you the wrong answer. Close, but you exchanged your trademark flavor for a slightly different variation: wild cherry.

“Bet you’d like to pop my cherry, Mr. Negan.” You goad him, ass firmly rooted to your spot. 

“You offering?”

“Absolutely begging,” You purr, matching his cheeky grin. The girls around you let out peels of smothered laughter. “Go on girls, I’ll be down soon.”

Alone with Negan, the flirtatious facade drops, allowing for the true nature of your relationship to become apparent.

“Little girl,” The tension is palpable, but rather than backing down like the rest of your classmates usually do, your back straightens, loving the bulging vein in his forehead and the husky tone of his warning. “I don’t think you know what you’re asking for.”

“You underestimate me, _Coach_.” Uncrossing your legs slowly, his eyes watch the movement before flickering up to your smug face. “I know exactly what I’m asking for. It’s just a shame you can’t take it.”

The shrill sound of a whistle echoes in the distance.

Neither of you moves.

“In a different world, Y/N.” He sighs, raking his hand through his windswept hair. “I’d be able to look at you for more than ten seconds without risking my ass going to jail.” 

His irises are like melted pools of chocolate. Which, you could admit had been the initial appeal of your PE teacher, but the depth behind them had been what had kept your fixation from passing. The slight twinkle in his eyes when he laughed. The way they hardened instantly, a flash of raw emotion behind his irises when he was upset. Almost as if someone had captured the element of lightning and let it run rampant within him. 

“I’ll be eighteen soon.” Your words are completely absent from your usual innuendos, any semblance of confidence completely put aside for now. The words are barely above a whisper and he has to strain himself to hear them before they’re swept away in the wind. 

One of the other coaches calls out to him in the distance, and he raises a hand, his eyes on you as he signals he’ll be there soon. 

Finally, he gives you a bittersweet smile, turning and making his way back down the bleachers. 

The taste of your lollipop mysteriously becomes sour. 

He hadn’t acknowledged the unspoken question. Not even for a moment. 

Now, you find yourself gazing into the same pair of chocolate colored eyes. Only this time the backdrop isn’t the chaotic scene of a busied football field. It’s your father’s office, during a meeting, as he attempts to secure a compromise with a neighboring colony. The Sanctuary, you’d heard about it over the dinner table but you’d never expected the visiting leader to be Coach Negan of all people, cloaked in leather and looking every part the badass you remember.

You can hardly contain your elation.

“If it isn’t Coach Negan!” You hardly pay any mind to the strained noise that leaves your father’s throat, signaling a moment of realization. “Well, well,” Motioning to a set of brawny men on either side of him, you note, “they’ve got you leading the horde, I see.” 

“I’ll be damned. _Y/N_?” Fuck, your name rolling off his tongue should be a certified sin. 

“Hold my lollypop. Will yah, mustache?” Passing your signature treat to the man beside Negan with the impressive handlebar mustache, you brace both arms on either side of his seat to get a better look at the man who’d been the object of obsession your entire high school career. 

He looks completely different, but six years will do that to a person. The creases around his eyes have deepened and the hairs at his temple are beginning to gray. Beneath your confident facade, you desperately search for some familiarity.

“Miss me, Cherry?” The flirtatious smile holds a slight edge and you think, you quite like the way his eyes openly roam the expanse of your body. 

There’s no reason to hide anymore. The mutual thought passes unspoken between you two as you openly eye-fuck each other in a room full of observant individuals.

“Miss you?” The fluttering of your eyelashes is only the icing on the cake, as you lean in close to breathe into his ear. He smells of menthols and leather, and the position gives him a straight shot down the front of your shirt. “Where’d you go, Coach? You never left my wet dreams.”

The creaking of a chair makes you both turn.

“Like what you see…?”

“Simon,” He cranes his head even further to get a better view of your ass, “and yeah, I do.”

“Well, too bad,” Licking your lips and lowering your voice so your oblivious father is none the wiser, you whisper with a luring tone, “because it’s all his. Right, Coach?”

“Back the fuck off, Simon.” His eyes harden minutely and Simon retracts instantly. Yes, there he was. If you weren’t sure then, you were now. 

“Coach?” Mustache finally queries.

“Y/N, if you’re about done?” Your father gives you a pointed look and you know that you’ll have to fill him in on your actions later. Your relationship with your father wasn’t very traditional. Being in the Army meant you never saw him much growing up. He was more a sibling then anything, an overprotective, older brother at that. 

He’d been stationed at Fort Belvoir and it’d only been pure chance that you’d found him the moment the world had gone to absolute shit. Your father was an excellent leader for all his flakiness during your childhood. Belvoir, your community, ran a tight ship under his watch and was apart of a much bigger network of rebuilt military bases spanning across the east coast. 

“Sorry, Dad. It’s just nice to see a friendly face.” He nods understandingly and in playing the role of the ever-doting daughter, you take your usual perch on his desk, waiting for the reason why he’d called you into his office in the first place. 

“Negan and his men are here to take a look around Belvoir, they’re interested in joining the network.”

“Smart move,” You comment, noting that Negan hardly pays attention to your father as he rattles on about agriculture and aqueducts. Instead, his pupils remain locked onto your roving tongue as it dwindles away at the lollipop in your grasp. Now more than ever did you appreciate your favorite treat.

“…but we can discuss this later, you must be very tired. My daughter will escort your men to the kitchen, show you where you’ll be staying for the night.”

“That’s me,” You give a mock salute, “glorified hostess at your service.”

With an exaggerated hand gesture on your part, the small group of eight men, begin to shuffle out the door. Really, men were like sheep. The sooner you’d figured that out, the sooner playing the field had become like second nature.

But there was only one man you’d ever really wanted, and it’s seemed that fate herself had played a considerable role in this one. 

Negan’s the last to stand, brushing past you in the doorway as he goes. 

“Y/N,” You barely peel your eyes away from the hypnotic sway of Negan’s ass to look your father in the face. “I want you on your best behavior. Don’t screw this up. I need him to trust us.”

You’re sure he’d said something along the lines of ‘don’t fuck this up’. But your one track mine had barely processed: ‘screw’ and ‘him’.

With pleasure.

“Don’t worry, Daddy.” With a small smile, you can’t help but cheekily blow a kiss as you shut the door. “I’ll show Coach Negan the best parts of Belvoir. _Promise_.“

* * *

“ _Oh_ , fuck!” Turning to get the key in the lock, you’re given a much-needed lungful of air and a moment of reprieve from Negan’s searching lips. Seeing that yours are out of reach, he changes the tactic of his aggressive campaign, conquering the newly exposed flesh of your neck as he pulls you tighter onto the knee wedged between your legs. 

“Cherry,” He breathes. The grip on your ass tightens, pressing you tighter against his groin.

Catching the key in its lock and with some slight maneuvering, you unlock the door, detangling yourself from his arms and backing further into the room. 

“ _Coach_.” You shuffle backward until your legs hit the edge of your mattress. With a sweeping gesture, you indicate. “My room.”

“All tours end here?” He kicks the door closed behind him, stalking forward. 

His leather jacket is the first to go. 

“Only for special guests.” Without preamble, you tug your bottoms down your legs, baring yourself to him.

Every hormonal filled fantasy that you’d ever had— _ever_ , rushes back to you simultaneously as he falls to his knees before you, shrugging off his shirt in a quick motion.

“Do you know how many times I thought of you like this,” He gazes up from under long eyelashes with a wolfish grin, pausing to let you confess, “between my legs and touching me? There was a permanent damp spot on my pillow.”

“I don’t think my dick was ever soft around you, Cherry. You and those damn lollipops.” He admits, settling on his ankles with an almost thoughtful expression. “Got any more?”

You point to your bedside table, and in a few seconds, he’s back between your legs with an unwrapped lollipop. You’d taken the time to remove the rest of your clothes and you sat, quite boldly in the buff, letting your old PE teacher take in the spectacle. The weight of his heated gaze settles on your flushed chest, slowly trailing the expanse of your taut stomach to your sopping wet pussy. 

“Suck this.” Leaning forward you do as he says, taking the sucker into your mouth, giving it your usual attention. The familiar taste of artificial cherries makes your mouth flood with saliva. It’s followed shortly after by a pang of pain. A cavity. 

Grasping a breast, he gives it the same treatment as the lollipop in your mouth. Dragging his wet tongue along the outer perimeter of your areola before taking the entirety of your nipple into his mouth with a soft suckling motion. The ripened bud stands swollen and at attention as he switches to the other. Throwing your head back, the pleas that fall from your lips come out slightly garbled around the temporarily abandoned lollipop. 

“You just loved to tease me with these didn’t you?” Shaking your head in agreement, you urge him to continue. “Goddamnit Y/N, I almost took you on those bleachers that day. Remember?”

“Uh, huh.” Less talkie, more _sucky_.

“Impatient.” He chides, rising on his knees so that you’re both at eye level. Removing the forgotten lollipop he softly requests against your lips, tasting the remnants on your tongue. “Lean back.”

Curious as to what he’ll do next, you eagerly recline, pushing all thoughts of your father’s disapproving face from your mind.

“Oh, fu—!” The sticky surface of the lollipop slaps your hardened clit causing your hips to buck. Startled you meet Negan’s cocky gaze, watching from beneath hooded eyes as he coats the lollipop in your juices before burying it within your core.

“Fuck,” He groans, watching your greedy center envelop the lollipop as he fucks you with it, “now you’re cherry flavored—inside and out, huh?”

He gently twirls the candy and the bulbous head of the sucker nudges against your g-spot causing you to cry out. The sensations and the low grunts Negan emits from the back of his throat sends shock waves up your spine as he presses the sugary concoction deeper within you. When he digs his palm into your mound it’s simply too much, sending you over the edge and clamping down on the candy.

It takes you a moment to realize that it’s you making those noises. 

Taking one side of the lollipop into your mouth, he takes the other, and together you taste the flavor of your essence until it falls completely forgotten onto the sheets. You’re both too entirely consumed in one another to notice.

“Fucking cherry flavored, Y/N.” Negan groans, palming his dick.

Gripping him closer your teeth travel to the corded muscle at his shoulder, sinking your teeth into the sun-kissed skin.

Mine. Mine. Mine. 

You repeatedly suckle the area before letting go with a pop to view your masterpiece. 

“Tell me, Y/N.” Fondling the dripping flesh between your thighs he cups your head to share a sucking kiss, pulling your tongue into his mouth until you aren’t sure where you end and he begins. “Tell me I can have your cherry next.”

“Afraid it’s too late to claim that cherry.” Four years ago, the back of a pickup and too much whiskey had snatched that fantasy away. Taking his palm you move it a little farther down, meeting his blossoming smirk with one of your own. “Although…I _think_ you might just get a second chance.”

“Thank fuck for second chances, huh?” He dives back between your thighs without another word, flicking your hardened clit with his tongue as he pulls you firmly onto his face. 

Oh, my.

Second chances, indeed.

**Author's Note:**

> Let me know what you think! Comments and kudos make me write better and faster! I just love hearing what you guys have to say. x


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